Ethyl bromoacetate → HCID 86670906, compound

HRID 403243Notes

Reaction equation

HRID 403243 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([I:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]([I:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 227146035-Chloro-2-iodopyridin-3-ol

Product 1

HCID 86670906HCID 86670906, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-chloro-2-iodopyridin-3-ol (15 g, 58.7 mmol) in N,N-dimethylformamide (150 ml) at 0° C. was added cesium carbonate (47.8 g, 147 mmol) and ethyl bromoacetate (14.7 g, 9.81 ml, 88.1 mmol) and the mixture was stirred at 23° C. for 18 h. Poured into brine, extracted thrice with ethyl acetate, dried the combined organic layer over sodium sulfate. Removal of the solvent in vacuum left an oil, which was diluted with tert-butyl methyl ether, washed with water and brine and dried over sodium sulfate. Removal of the solvent in vacuum left a light brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the ethyl 2-(5-chloro-2-iodopyridin-3-yloxy)acetate (17.3 g, 50.7 mmol, 86.3% yield) as a light brown solid. MS (ISP): m/z=341.9 [(M+H)+] and 343.9 [(M+2+H)+].

Workup

  1. extractionextracted thrice with ethyl acetate
  2. dry with materialdried the combined organic layer over sodium sulfate
  3. customRemoval of the solvent in vacuum
  4. waitleft an oil, which
  5. additionwas diluted with tert-butyl methyl ether
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent in vacuum
  9. waitleft a light brown oil, which
  10. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-f3b3ed10c9aa4380b4bb5f7b6587b7bc
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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